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Pregled bibliografske jedinice broj: 492121

Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine


Užarević, Krunoslav; Rubčić, Mirta; Stilinović, Vladimir; Kaitner, Branko; Cindrić, Marina
Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine // Journal of molecular structure, 984 (2010), 1/3; 232-239 doi:10.1016/j.molstruc.2010.09.034 (međunarodna recenzija, članak, znanstveni)


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Naslov
Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine

Autori
Užarević, Krunoslav ; Rubčić, Mirta ; Stilinović, Vladimir ; Kaitner, Branko ; Cindrić, Marina

Izvornik
Journal of molecular structure (0022-2860) 984 (2010), 1/3; 232-239

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
dehydroacetic acid; keto-enol tautomerism; asymmetric Schiff bases; resonance-assisted hydrogen bond; crystal engineering

Sažetak
Reaction of dehydroacetic acid and p-phenylenediamine afforded a monosubstituted Schiff base, I, with the other amino group free. In further reactions with various salicylaldehyde derivatives, I served as a precursor for synthesis of asymmetric bis-Schiff bases. The synthesized compounds are thus comprised of 2 subunits, dehydroacetic (dha) and salicylidene (sal) units, which are bridged by the phenylene linker. All products were investigated by means of elemental analysis, FT-IR and NMR spectroscopy, DSC, thermogravimetric analysis, powder X-ray diffraction and, when possible, by single crystal X-ray crystallography. Structural and spectroscopic studies revealed that in the bis-products, the dha subunit adopts the keto-amino tautomeric form, while the sal subunit adopts the enol-imino form. Tautomeric forms were not affected if a methoxo group was introduced on the salicylidene ring. Both tautomeric subunits are stabilized by strong resonance-assisted hydrogen bonds, RAHB. The two subunits of the prepared bis-Schiff bases predominantly retain in solution the same tautomeric forms as found in the solid state.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1191342-1082 - Novi kompleksni spojevi i materijali-kemijski i biološki katalizatori (Marina Cindrić, )
119-1193079-3069 - Novi organski i koordinacijski spojevi - sinteza i suodnos struktura-svojstvo (Branko Kaitner, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

Citiraj ovu publikaciju

Užarević, Krunoslav; Rubčić, Mirta; Stilinović, Vladimir; Kaitner, Branko; Cindrić, Marina
Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine // Journal of molecular structure, 984 (2010), 1/3; 232-239 doi:10.1016/j.molstruc.2010.09.034 (međunarodna recenzija, članak, znanstveni)
Užarević, K., Rubčić, M., Stilinović, V., Kaitner, B. & Cindrić, M. (2010) Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine. Journal of molecular structure, 984 (1/3), 232-239 doi:10.1016/j.molstruc.2010.09.034.
@article{article, year = {2010}, pages = {232-239}, DOI = {10.1016/j.molstruc.2010.09.034}, keywords = {dehydroacetic acid, keto-enol tautomerism, asymmetric Schiff bases, resonance-assisted hydrogen bond, crystal engineering}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2010.09.034}, volume = {984}, number = {1/3}, issn = {0022-2860}, title = {Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine}, keyword = {dehydroacetic acid, keto-enol tautomerism, asymmetric Schiff bases, resonance-assisted hydrogen bond, crystal engineering} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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